The present invention relates to the production of an alkene mono-ol and also to the synthesis of citric acid.
Production of alkene mono-ols is disclosed in U.S. Pat. No. 3,574,773. Thus, according to Example 4 of U.S. Pat. No. 3,574,773, formaldehyde is reacted with isobutene to obtain mono-ol.
U.S. Pat. No. 3,692,848 discloses the production of alkenediols from mono-ol by reaction of the mono-ol with formaldehyde.
Commonly assigned patent applications Ser. Nos. 379,511 and 427,176 disclose the preparation of alkenediols, e.g., 3-methylene-1,5-pentanediol (alpha-diol) and 3-methyl-2-pentene-1,5-diol (beta-diol) by reaction of isobutene with formaldehyde. Commonly assigned Ser. No. 491,987 discloses the conversion of alpha-diol to citric acid in an oxidation process. The disclosures of these three applications are incorporated herein by reference, particularly in that they relate to preparation of alpha- and beta-diols, and to conversion of alpha-diol to citric acid.
In view of the present invention, we have also located an article by G. Ohloff in Chem. Ber., Vol. 93, p. 2673 (1960) which discloses the thermal (temperature = 350.degree. C.) splitting off of formaldehyde from a cyclic beta-hydroxy olefin. Also, Smith and Yates in J. Chem. Soc. (1965), p. 7242, disclose pyrolysis of but-3-en-1-ol (370.degree. C.) to obtain propene and formaldehyde and the pyrolysis of pent-4-en-2-ol to produce propene and acetaldehyde.
The thermal condensation of formaldehyde with an olefin is disclosed in F. Asinger's book Monoolefins -- Chemistry and Technology, Pergamon Press (1968), p. 719.